Hydrochloric Acid → HCID 22396895, compound

HRID 2306986Notes

Reaction equation

HRID 2306986 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:5]([Cl:31])=[CH:6][C:7]2[C:8]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19][C:9]=3[N:10]([CH2:13][C:14]([O:16]CC)=[O:15])[C:11]=2[CH:12]=1.Cl>O.C1COCC1>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][C:8]2[C:7]3[CH:6]=[C:5]([Cl:31])[C:4]([Cl:3])=[CH:12][C:11]=3[N:10]([CH2:13][C:14]([OH:16])=[O:15])[C:9]=2[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22396677HCID 22396677, compound

Product 1

HCID 22396895HCID 22396895, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of KOH (0.17 g, 3.0 mmol) in H2O (10 mL) was added to a solution of tert-butyl 8,9-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (1.00 g, 2.27 mmol) in THF (15 mL). The mixture was heated at 60° C. for 2 h. The reaction was then cooled to rt, acidified with 10% aqueous HCl, and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated to give crude acid (1.03 g, 110%): 1H NMR (300 MHz, CDCl3) δ 7.50 (s, 1H), 7.26 (s, 1H), 4.73 (s, 2H), 3.74 (m, 2H), 3.67 (m, 2H), 2.89 (m, 4H), 1.47 (s, 9H); MS(ESI+) m/z 410.9.

Workup

  1. temperatureThe reaction was then cooled to rt
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a27213607247489c9e7c37a486f62bfc
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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